Department of Chemistry, New York University, New York, NY 10003, USA.
Chem Soc Rev. 2010 Apr;39(4):1325-37. doi: 10.1039/b901977b. Epub 2010 Mar 4.
This tutorial review examines recent developments involving use of Copper-catalyzed Azide-Alkyne [3 + 2] Cycloaddition (CuAAC) reactions in the synthesis, modification, and conformational control of peptidomimetic oligomers. CuAAC reactions have been used to address a variety of objectives including: (i) ligation of peptidomimetic oligomers; (ii) synthesis of ordered "foldamer" architectures; (iii) conjugation of ligands to peptidomimetic scaffolds; and (iv) macrocyclization of peptidomimetics using triazole linkages as conformational constraints. Variations in synthesis protocols, such as the use of different solvent systems, temperatures and copper species are evaluated herein to present a range of variables for the optimization of CuAAC reactions. The overall objectives of these studies are assessed to highlight the widespread applications of the products, which range from bioactive ligands to new materials.
本教程综述考察了在合成、修饰和肽模拟寡聚物构象控制中涉及铜催化叠氮-炔烃 [3+2] 环加成（CuAAC）反应的最新进展。CuAAC 反应已被用于解决各种目标，包括：（i）肽模拟寡聚物的连接；（ii）有序“折叠体”结构的合成；（iii）配体与肽模拟支架的缀合；以及（iv）使用三唑键作为构象约束进行肽模拟物的大环化。本文评估了合成方案的变化，例如使用不同的溶剂系统、温度和铜物种，以提供一系列变量来优化 CuAAC 反应。评估这些研究的总体目标是突出这些产物的广泛应用，从生物活性配体到新材料。
